


A Learning Experience

by femmefatales (orphan_account)



Series: A Learning Experience [1]
Category: Supernatural
Genre: Dad!Dean, Explicit in later chapters, M/M, Wincest - Freeform, Wincest AU - Freeform, nanny/single parent au, they aren't brothers in this
Language: English
Status: In-Progress
Published: 2014-09-29
Updated: 2014-11-30
Packaged: 2018-02-19 05:46:20
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 3,889
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2376977
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/femmefatales
Summary: <blockquote class="userstuff">
              <p>How Dean Winchester ended up with a kid is beyond him. When Sam Winchester, law school student and part-time nanny enters his life, Dean might have a shot at a real family after all.</p>
            </blockquote>





	1. Sam, the Nanny

How Dean Winchester ended up with a kid is beyond him. 

These last couple of months are all muddled together in his mind. He’d knocked up a girl after meeting her at a bar one night and the next thing he knew, she’d shown up at his doorstep with smeared mascara and tears streaming down her face. She’d wanted to get rid of the kid; said it’d fuck up her life. And Dean wasn’t about to let that happen so he swore to her that he would raise it. And she’d agreed.

A little less than a week after giving birth to Dean’s son (he’d named him Robert after the lead singer of Led Zeppelin) she took off without so much as a phone number. And now Dean was stuck with a five-week-old little boy.

And Dean loves Robert, he really does. There’s something in his big blue eyes that makes Dean feel like he has an actual purpose in this world. He actually means something; a tiny little life is in his hands. But he hates the helplessness he feels when he can’t get him to stop crying or figure out what’s wrong or how to make it better. 

Then he meets Sam.

Dean’s at the supermarket, carrying Robert in one of those weird baby-sack things that straps across his chest. He's in the baby isle trying to decide on the best brand of formula to buy and the kid won’t stop crying—well, screaming, and he’s starting to get some pretty weird looks. Dean panics, trying to figure out what he’s doing wrong. He’d fed Robert less than an hour ago and changed his diaper right before they left. So why was Robert freaking out?

“Shh, Daddy’s here, alright?” Dean says softly, beginning to hum Nothing Else Matters by Metallica and bouncing him up and down. He curses quietly when Robert’s screams only increase in volume.

“Hey, man. Neck support. You gotta make sure he’s sitting up right.”

Dean whirls around and almost smashes into the big guy who’d given him the advice. 

“What?”

“Neck support. Here, let me help.” The man reaches forward and adjusts Robert’s position. Dean stares up at him in awe when Robert’s cries immediately cease. Is this guy a wizard? Dean wonders.

“How’d you do that?” He asks. The man laughs.

“Babies get grumpy when they aren’t comfortable. I’m Sam, by the way.” The man reaches out his hand and it takes Dean a moment to shake it after he realizes how good-looking this guy is. He has shaggy brown hair framing his sharp jawline and doughy hazel eyes. His muscular build makes Dean, who's decently fit, feel scrawny. Now, Dean doesn't swing that way, but if he had to make an exception he figures it'd be for a guy like that. 

"Dean. Dude, you just saved my ass from getting kicked out of here. Thanks." He says, breathing out a sigh of relief.

Sam smiles at Dean. “Anytime, man. He your first?” He asks, nodding at baby Robert, who is now giggling and making a variety of cooing noises. 

"Yeah. In case you couldn’t tell." Dean huffs out a self-deprecating laugh. 

"You’re actually pretty good with him. You giving Mom a break or something?"

Dean chuckles and shakes his head. “You could say that. Mom ain’t really in the picture.”

Sam’s smile immediately falls. “Oh. That must be pretty hard.”

"It’s definitely a learning experience. But hey, at least now I have a reason to get my shit together. How do you know so much about kids, anyway? You have any?"

"Nah, I’m actually a part-time ‘nanny’, I guess you could say. I’m in law school right now and I gotta pay for it somehow. I figured since I’ve always been good with kids, why not?"

"Oh, nice. You got a card or something?" Dean asks. He could really use some kind of help with Robert and Sam seems to know what he’s doing. 

Sam looks startled for a moment and then reaches into his back pocket.

"Yeah, sure," He hands the card to Dean, who’s practically beaming at this point. 

"Only 10 bucks an hour?"

"Uh, yeah. Were you expecting more?"

"Kind of, but I’m not complaining." 

“Awesome. You can give me a call whenever you need some help and I’ll try to be there.” Sam says. 

"Great. Thanks again for earlier."

~~

That night when Dean can’t get Robert to fall asleep, he dials Sam’s number.


	2. A Huge Favor

**Summary for the Chapter:**

> Sam visits Dean's apartment.

**Notes for the Chapter:**

> Hey guys! I've continued the story since a few people on tumblr and on here were asking me to. Hope you enjoy it! And if you're just in this for the smut, well, there will be smut. But most likely not until later chapters.  
> Thank you so much for reading and I really appreciate comments/reviews!

Sam’s POV  
Sam’s phone rings at 8:30 PM that night. He’s already changed into his pajama pants and is in the middle of a Criminal Minds marathon, so he thinks twice before picking it up. Whatever it is, it can probably wait, right?  
But then Sam sees an unknown number and remembers the insanely hot single Dad from earlier, Dean, and answers it.  
“Hello?”  
“Hey, Sam. It’s Dean, the guy from the supermarket.” A baby wails in the back round and Sam holds the phone away from his ear.  
“Hey, yeah, I remember.”  
“I know it’s pretty late, but remember how you told me to call whenever I needed help? Well, uh. I need help.” Dean sounds desperate and Sam represses a laugh.  
“No worries,” Sam says, feeling a little too happy about this late-night phone call. He doesn’t even know the guy, for Christ’s sake. “Have you changed his diaper recently?”  
“Yep. Fed him earlier too.”  
“Strange. Need me to come over? I mean, if you’re comfortable with that.” Sam had long ago memorized a list of possible reasons babies cry, but why would he pass up the opportunity of seeing Dean in person again?  
“You’d do that? Thanks, man. You’re a lifesaver.”  
Dean gives Sam his address and the two exchange their goodbyes. As Sam changes out of his pajamas and into a T-shirt he feels a twinge of guilt. Sure, he’s helping the guy out, but he has ulterior motives. And obviously this guy is straight. He has a freakin’ kid.  
Sam shrugs it off and hops in his car anyway. 

~~~  
Sam knocks on the door to Dean’s apartment. He stands there for a moment and then the lock clicks open. A delicious smell hits Sam immediately and he wonders momentarily if Dean can cook.  
“Hey. Thanks again for coming.”  
Sam swallows when he sees Dean. God, was he this attractive earlier? His hair is slicked back and he’s wearing a white T-shirt and jeans that he probably wouldn’t have thought about wearing if he knew Sam’s sexual orientation.  
“No problem. Robert still giving you a hard time?”  
Sam’s question is answered when he hears a high pitched wail. Dean laughs ruefully and invites Sam inside.  
This apartment really doesn’t look like it belongs to a guy with a baby, Sam thinks as he looks around. There’s a small living room with a wooden table and two chairs. An old radio is mounted on a shelf packed full of CDs right next to a small leather couch. Conjoined with this room is the kitchen, which Sam can barely see; he can, however, still smell whatever’s cooking and it’s making his mouth water.  
Dean leads him down a tiny hallway and Sam realizes that he hasn’t seen one picture yet. Doesn’t Dean have a family?  
And then they’re in the bedroom. There’s one huge, unmade, king-sized bed in the center, and aside from a signed Metallica poster from 1996, there’s nothing on the walls. It takes Sam a minute to notice the crib in the opposite corner of the room despite the loud cries emitting from it.  
“Nice place,” Sam practically screams over Robert’s wails.  
“Thanks,” Dean says, leading Sam over to the crib. Robert is wrapped in a few blankets and has a blue beanie on his head. Sam thinks for a minute that this is probably the cutest kid he’s ever seen, with chubby cheeks and impossibly large blue eyes.  
“What’s the matter, kiddo?” Sam asks softly, peering down into the crib. Dean looks at Sam helplessly.  
“I’ve tried everything but he won’t shut up. It’s gonna drive me crazy.”  
Sam thinks for a minute.  
“What’s the temperature in here?”  
Dean looks at Sam strangely.  
“I’ll check the thermostat,” He walks into the hallway and returns a moment later. “It’s seventy-five. Why?”  
Sam smiles. “Robert’s too hot. You have him all bundled up and it’s seventy degrees in here.”  
Dean’s look is one of pure horror and confusion. “But aren’t you supposed to keep babies warm? They’re babies!”  
“Yeah, well. Babies are high-maintenance. They cry about everything. Mind if I take a blanket or two off?”  
Dean nods and Sam gently scoops Robert into his arms and removes the top blanket. This proves to be a repeat of today’s previous events as he stops crying immediately.  
“Jesus,” Dean says, completely bewildered. “You’re a friggin’ baby whisperer.”  
Sam laughs softly and rocks Robert back and forth.  
“Guess you could say that, yeah. See? He’s already sleeping.” Sam looks down at the baby in his arms who’s eyes had closed just moments ago.  
“How’d you get to be so great with kids?” Dean asks, still looking at Sam like he’s some kind of alien.  
“I have two brothers and a sister, all younger than me. And a mom and dad who don’t really give a shit. So I helped out a lot.”  
“Geez,” Dean says. Sam’s about to ask if Dean has any siblings when his thoughts are interrupted. “Hey, you hungry? I made some barbecue ribs if you want any.”  
So that’s what smells so good, Sam thinks.  
“Nah, I shouldn’t be eating your food--“  
“Dude, I have a shitton of leftovers. I always cook way more than I need.”  
Dean’s smile is blinding and Sam practically feels his legs turn to jelly beneath him.  
“Alright.”  
He sets Robert down in his crib and lets out a sigh of relief when the baby doesn’t do so much as make a sound.

 

~~~~  
A few minutes later Sam is biting into the best barbecue ribs he’s ever tasted. Meals like this make him wish more than anything that he could cook. He can’t even make a bowl of Mac N’ Cheese without catching something on fire, much less create something as delicious as this.  
“That good, huh?” Dean’s smirking at Sam who just then realizes that he’s been eating like a complete pig.  
“Sorry,” He says, face flushing. “I just haven’t really had a decent meal lately. Unless you count ramen noodles.”  
Dean laughs. “How old are ya’ anyway? You said you were in law school right?”  
“Just turned twenty-one. It’s my first year of law school, actually.” Sam replies. Dean raises his eyebrows.  
“Only twenty-one?”  
“Yep. What, is that surprising?”  
“I’d have guessed somewhere around twenty-five.”  
“Oh. Thanks, I guess,” Sam tries to figure out whether or not this is a compliment and fails. “What about you?”  
“Twenty-six.”  
That’s about how old Dean looks, Sam thinks. There’s something in his eyes, though, that gives off the impression that he’s been through a lot in his lifetime.  
“If you don’t mind me asking, what do you do?” Sam asks. He worries for a moment if he’s crossed some sort of line with the personal questions, but Dean answers him immediately.  
“I own a mechanics shop down the road. It belonged to my dad, and now it’s mine.”  
Sam feels the urge to ask what happened to Dean’s father but represses it.  
“A mechanics shop? Sounds pretty difficult.”  
“Nah, I’ve got good employees and I know what I’m doing. It has been harder lately though, with Robert and all.”  
“Well if you ever need a sitter you know who to call,” Sam says, putting on one of his most charming smiles.  
“Yeah. Thank God for that. I’ve been thinking of hiring some kind of a sitter but I didn’t want to trust someone completely random with my kid, ya know?”  
“Am I not ‘completely random’?” Sam asked.  
“Well yeah. But I can tell you’re a good guy who knows a lot about kids,” Dean says, looking at Sam as if he’s sizing him up.  
“Thanks,” Sam says. He figures he should probably get home and study even though he would’ve continued talking to Dean for hours if he could. “I should probably get going, but the food was awesome.”  
“So soon? Alright. How much do I owe you?” Dean asks as he and Sam walked to his front door. Sam laughs.  
“Owe me? Dude, I literally just helped you put your kid to sleep and you made me food. I don’t think you owe me anything.”  
“Whatever you say, man, but you did me a huge favor.”  
“Any time. Guess I’ll see you around then?” Sam asks, trying to keep the hope out of his voice.  
“Definitely.”  
As Sam is on his way out, he notices an acoustic guitar leaning on the sofa and idly wonders if Dean can play.  
On his way home, all Sam thinks about is that deep, rumbling voice and charming smile of his. Sam swears he’s never met a guy so attractive in his life.  
Christ, what am I getting myself into? Sam thinks as he adds Dean’s number to his contacts.


	3. Hop In, Kid

**Summary for the Chapter:**

> Dean goes to work. Then he receives an unexpected phone call.

**Notes for the Chapter:**

> Hey guys! I had some people who really wanted me to continue this, so here you go. I'm in deep now, and I'm not gonna stop. Thanks for sticking with me! <3 I will love you forever if you leave a comment telling me what you think.

Chapter 3  
Dean is jolted awake by the obnoxious beeping of his alarm clock at 9:05 AM. He decides then that the blaring, high-pitched tone is probably his least favorite sound on the planet. He shuts it off quickly, thanking God that it didn’t wake up Robert who had kept him up practically all night. Dean would’ve allowed himself an extra hour of sleep if it wasn’t for the fact that today is Friday, meaning more customers and more business.  
Dean sits up and rubs his eyes, groaning at the soreness in his neck. Must’ve slept funny, he thinks, stretching gingerly and standing up. The wood floor is cold on his feet as he walks over to Robert’s crib to check on him.  
Robert is snoozing away, curled up in a little ball and snoring softly. His big eyes are closed and Dean can see the shadows of his eyelashes on his chubby cheeks. He reaches his hand down into the crib and gently strokes the small tuft of blonde hair on his son’s head, marveling at the softness of it. Dean is almost knocked off his feet by the huge wave of pure, unadulterated love that crashes into him then. He loves his son more than anything and Dean is sure that Robert is the best thing that has ever happened to him.  
God, who would’ve thought? Dean never even wanted kids, never even considered the possibility. But here he is, gushing over this tiny, beautiful kid who had entered his life unannounced.  
He reluctantly draws his hand away and goes to get dressed. His closet is full of old T-shirts, flannel, and jeans, but he figures that he should at least look semi-decent today. Dean is the owner after all. So he ends up choosing a pair of khaki pants (much to his distaste) and a blue polo. Then he brushes his teeth, slaps on some aftershave, and runs a comb through his hair.  
Then he has to go wake up Robert. He has no choice but to to bring him along (he figures he's bothered that college kid Sam enough in the last two days.) Plus, Robert is a customer-magnet. His cuteness lures people in and is extremely good for business.  
~~  
Dean is greeted by one of his favorite smells, paint and oil, when he enters his shop. Robert is sitting contentedly in the baby-sack strapped across Dean’s chest. This time, he makes sure that his son has proper neck-support.  
“EVERYONE, PLACES!!” Dean hears someone yell. “BOSS IS HERE!”  
This is followed by a fit of laughter. Dean rolls his eyes when Ash, his manager, walks up to meet him at the counter. His mullet is slicked-back today and Dean figures that this is probably an attempt to look more professional.  
“I kid, I kid. Everyone’s workin’ their asses off, as usual,” Ash says. “Look who it is! Hey, Robster!”  
Robert coos and reaches a tiny hand out toward Ash. Dean chuckles.  
“Yeah, yeah,” Dean replies, looking down at Robert. “We all know how much you wish Ash was your dad. Hey, man. Everything going smoothly?”  
“Yup. Lots of customers today. We’ve got our hands full.”  
“Awesome. I’d offer to help out, but you know.”  
“It’s all good,” Ash says. “Jo’s working harder than anyone, though. Glad you decided to hire her.”  
Dean beams. Jo is their only female employee and probably their hardest worker. She always shows up on time, always tries her best, and does a damn good job with her repairs. Dean had already had enough employees when she'd asked him for a job, but she was so determined that Dean couldn’t help but hire her.  
“So am I. I’m gonna go see how everyone’s doing,” Dean says, nodding at Ash and walking into the repair garage.  
Their are four cars currently being repaired, which is the maximum that can fit in the garage at once. Each of Dean’s employees, Jo, Andy, and Castiel are hard at work.  
“Hey guys,” Dean says, making his presence known. Andy knocks his head on the bumper of the car he is working on and Dean cringes.  
“Shit! Uh, hey, Boss.” Andy says, flush spreading across his stubble-covered cheeks.  
Jo rolls herself out from under a silver Prius. A streak of grease is on her cheek. “Hey.”  
Castiel doesn't even budge. Dean hears a muffled “hello” from under the car he's working on.  
“Anyone need any pointers?” Dean asks. He may not be doing any of the actual work, but he knows cars better than anyone there. His dad had taught him everything he knew.  
Dean ends up showing Andy the easiest way to fix a pick-up truck’s transmission and helping Castiel out with a broken muffler on a 1993 Ford Fiesta, taking breaks to feed Robert in between. Jo is usually too prideful to ask Dean for help, and today is one of those days.  
Before he knows it, it's 2 PM and Dean is ready to head home for the day. It seems like his employees have everything under control and that his presence is no longer needed.  
~~  
Later that day, Dean sits on the couch and plays with Robert. He's still too young for toys, but Dean had heard somewhere that it was good to talk to kids and play with them right from the start. So he'd plugged in his iPod, started playing some quiet Led Zeppelin, and is talking to Robert about how he was going to start teaching him guitar the moment he takes his first steps.  
Dean sighs when he hears the blaring guitar solo that is his ringtone. He picks Robert up, places him on his shoulder, and answers.  
“Hello?” Dean asks.  
“Uh, hey. Sorry to bother you.” It's Sam, the nanny kid. His voice is tinged with panic and Dean wonders what reason he could have for calling him. Not that he minds.  
“Hey, no problem. You alright?”  
“I, uh, yeah. I’m fine. But I remember you said you own a car repair shop. Right?”  
“I do.”  
“So... you know a lot about cars?” Sam asks tentatively.  
“Yeah, I know everything there is to know. Why d’you ask?”  
“Well, um, I’m really sorry to inconvenience you like this but you’re the only person I knew who might be able to help,” Sam takes a breath. “My car.. it’s.. I don’t know. It stopped working and I’m in the middle of the road. I know I didn’t run out of gas, I just filled the tank. But it won’t start up again.”  
“Your engine’s probably shot. You got AAA?”  
Dean hears Sam swallow.  
“It’s expired.”  
“Oh, shit,” Dean says, feeling a touch of worry for the kid. “You need someone to pick you up?”  
“What? Oh, no, you don’t have to do that. I was just hoping, maybe you could tell me what to do and how to fix it so I could get going again--“  
“If it is your engine, that’s not happening. I can come get ya, it’s not a big deal. I mean, if you don’t already have someone else you can call,” Dean doesn't understand why he's actually really hoping that Sam will accept his offer.  
“I, um, I don’t. Everyone close by is in class right now.”  
“That’s right, you’re a college boy. Alright, I’m on my way,” Dean says, grabbing his brown leather jacket off the coat hanger and setting Robert down in his crib temporarily.  
“Are you really going to come? Thank you, thank you so much,” Sam replies, clearly relieved.  
“Sure thing, man. Where are you?”  
“You know Cresbi Street? It’s right by that old antique shop.”  
“Yeah, yeah, I know where that is. Hope you don’t mind if Robert comes along.”  
“Not at all. Thank you, again.”  
Dean smiles.  
“See you in a few.”  
~~  
Sam’s POV  
Dean shows up about ten minutes after Sam had called. He pulls up behind him in an old, black car. The sun reflects off of its glossy surface and Sam swears that it's the coolest car he's ever seen. Something about it really suits Dean; he looks amazing driving it.  
Sam hops out of his car and Dean does the same. Dean waves and smiles at Sam who's temporarily blinded by how ridiculously handsome the other man is.  
“Hey, glad to see you’re still alive,” Dean says. Sam chuckles.  
“Yeah, I am too. I got some guy to help me push my car off the actual road,” Sam says, noticing how insanely green Dean’s eyes are. “Thank God.”  
“You want me to take a look at it?” There's obvious excitement in Dean's voice.  
“Go for it,” Sam watches as Dean makes his way over to the hood and pops it open. He tries to keep his eyes away from Dean’s extremely nice ass (figures), which proves to be an impossible task. Jesus.  
“Your engine overheated,” Dean’s voice brings Sam back to reality. “Dude, do you even take your car in for maintenance? It’s a disaster in here.”  
“Uh,” Sam says. “No. My dad always told me those places were rip-offs.”  
Dean smirks. “That explains it. See, your dad was right. But it’s not a rip-off if you go to the right place.”  
“How can I know which is the ‘right place’?” Sam asks.  
“Well, you can always ask me. Car mechanic, remember?” Dean says. “I would tell you to come to my shop for oil changes and stuff, but we’re more about intensive repair than minor stuff like that. But, uh, you’re gonna have to replace your engine. Which I can help you with. Unless you’re just gonna by a new car.”  
Sam feels happiness bloom in his chest at the prospect of Dean fixing his car for him. He was planning on just throwing this old piece-of-crap Toyota away, but now he's having second thoughts.  
“How long would it take for you to fix it?”  
“Bout a month or two, depending on how busy we are.”  
Sam can't help but smile then.  
“Alright. I’ll definitely be visiting your shop soon.”  
Dean beams.  
“Awesome,” Dean says. “Now hop in, kid.”


End file.
